If you’re a fan of witty banter and sparkling chemistry, it’s only natural to search for how to lose a guy in 10 days similar movies. Whether you love the enemies-to-lovers dynamic, quirky romantic bets, or just the pure fun of romantic comedies, there are plenty of movies that capture the same magic. This guide is for anyone looking for movies like How to Lose a Guy in 10 Days—perfect for a girls’ night, date night, or solo laughter binge.
Below you’ll find a carefully curated list of the top 10 similar movies to How to Lose a Guy in 10 Days—each one offering hilarity, romance, and just enough mischief to keep you hooked.
10. She’s All That (1999)
This classic teen rom-com kicks off with a high school bet: can popular jock Zack (Freddie Prinze Jr.) turn introverted Laney (Rachael Leigh Cook) into prom queen?
What starts as playful manipulation quickly leads to real emotions, identity crises, and genuine transformation.
Like How to Lose a Guy in 10 Days, it explores the gray area between games of the heart and authentic connection.
9. Hitch (2005)
Will Smith stars as Alex “Hitch” Hitchens, a legendary New York City dating guru. He helps awkward clients win over their crushes, all while struggling to woo the sharp and skeptical journalist Sara (Eva Mendes).
The film offers a clever look at dating misadventures, honest self-reflection, and the awkward charm of falling in love. Its blend of romance, comedy, and heart puts it high on any list of movies like How to Lose a Guy in 10 Days.
8. The Wedding Planner (2001)
stars as the meticulous Mary Fiore, whose professional life as a wedding planner is thrown into chaos when she falls for a handsome doctor—who just happens to be the groom in her latest wedding contract.
ALSO READ: The 10 Worst Movies Of The 90s (& Where To Watch Them)
What follows is a charming tangle of near-misses, slapstick encounters, and the chemistry between J.Lo and Matthew McConaughey, who is also the star of How to Lose a Guy in 10 Days.
If love triangles and mistaken identities are your thing, this is a must-see.
7. Bridget Jones’s Diary (2001)
This British rom-com classic features Renée Zellweger as Bridget, a lovable singleton navigating awkward moments, cringe-worthy dates, and a love triangle between charmingly roguish Daniel (Hugh Grant) and quiet but steadfast Mark (Colin Firth).
The film’s brutal honesty and relatable blunders resonate, making it essential viewing for anyone searching for how to lose a guy in 10 days similar movies.
6. 27 Dresses (2008)
Sandra Bullock and Ryan Reynolds light up the screen with their electric comedic timing in this beloved fake-relationship romp. Margaret, a hard-nosed book editor facing deportation, forces her assistant Andrew to marry her for a green card.
The two embark on a hilarious trip to Alaska, where family antics, a sweet grandma (Betty White!), and unexpected feelings make for a thoroughly entertaining journey.
If you crave chemistry and mistaken motives, this is a perfect fit for fans of movies like How to Lose a Guy in 10 Days.
5. A Perfect Pairing (2022)
What sets this movie apart is its ensemble cast and intertwined love stories. Steve Carell plays Cal, a heartbroken dad rediscovering dating with the help of suave Jacob (Ryan Gosling).
Meanwhile, Emma Stone’s character brings her own twist to the tangled web.
The film expertly balances laugh-out-loud moments with poignant scenes about vulnerability and forgiveness. If you love romantic mischief and genuine chemistry—hallmarks of how to lose a guy in 10 days similar movies—this one delivers.
4. The Hating Game (2021)
A more recent addition to the “enemies to lovers” canon, The Hating Game stars Lucy Hale as ambitious Lucy and Austin Stowell as her equally driven (and infuriating) office rival, Joshua.
Their daily sparring is loaded with sexual tension, leading to a series of hilarious dares and accidental confessions.
Like How to Lose a Guy in 10 Days, it’s packed with witty back-and-forth, passionate arguments, and those swoon-worthy moments that make romantic comedies irresistible.
3. Crazy, Stupid, Love (2011)
What sets this movie apart is its ensemble cast and intertwined love stories. Steve Carell plays Cal, a heartbroken dad rediscovering dating with the help of suave Jacob (Ryan Gosling).
Meanwhile, Emma Stone’s character brings her own twist to the tangled web. The film expertly balances laugh-out-loud moments with poignant scenes about vulnerability and forgiveness.
If you love romantic mischief and genuine chemistry—hallmarks of how to lose a guy in 10 days similar movies—this one delivers.
2. The Proposal (2009)
Sandra Bullock and Ryan Reynolds light up the screen with their electric comedic timing in this beloved fake-relationship romp.
Margaret, a hard-nosed book editor facing deportation, forces her assistant Andrew to marry her for a green card.
The two embark on a hilarious trip to Alaska, where family antics, a sweet grandma (Betty White!), and unexpected feelings make for a thoroughly entertaining journey. If you crave chemistry and mistaken motives, this is a perfect fit for fans of movies like How to Lose a Guy in 10 Days.
Honorable Mentions
- The Ugly Truth: Battle-of-the-sexes banter and unexpected romance.
- Just Go With It: Adam Sandler and Jennifer Aniston deliver a blend of fake relationships and real feelings.
- Love Actually: Interwoven stories of love—in all its chaos—make this a holiday favourite.
- Set It Up: Office matchmaking leads to adorable—and chaotic—romance
1. 10 Things I Hate About You (1999)
A modern update on Shakespeare’s The Taming of the Shrew, this film is far more than just a teen romance. Julia Stiles plays the stubborn and fiercely independent Kat Stratford, while Heath Ledger’s charismatic Patrick is hired to woo her so her younger sister can date.
Their evolving relationship, driven by clever dialogue and memorable moments (including THAT poem), feels authentic and full of heart.
As with How to Lose a Guy in 10 Days, enjoy the witty banter and slow build from adversaries to something much more meaningful.
Why These Films?
- The sparkling chemistry between leads.
- Plot-driven romance: bets, fake relationships, or reluctant pairs.
- Laugh-out-loud comedic moments mixed with heartfelt emotion.
- Exploration of dating mishaps and miscommunications.
Whether you prefer older classics or modern hits, you’ll find plenty of movies like How to Lose a Guy in 10 Days to binge next
Related to How To Lose A Guy In 10 Days Similar Movies
If you still need more content like this, then all you need to do, is check out what we have below on offer.
We just know, if you loved this post, that you’ll enjoy those films, really, it’s a no-brainer.
Please like this post, share it with your friends, and leave a comment below.
